GB815140A - Improvements in or relating to esters of metaboric acid - Google Patents
Improvements in or relating to esters of metaboric acidInfo
- Publication number
- GB815140A GB815140A GB2244457A GB2244457A GB815140A GB 815140 A GB815140 A GB 815140A GB 2244457 A GB2244457 A GB 2244457A GB 2244457 A GB2244457 A GB 2244457A GB 815140 A GB815140 A GB 815140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- metaborate
- butyl
- chloroboronate
- propyl
- orthoborate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 3
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 title abstract 3
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 16
- 238000000034 method Methods 0.000 abstract 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- BRCRFYDCLUTJRQ-UHFFFAOYSA-N chloroboronic acid Chemical compound OB(O)Cl BRCRFYDCLUTJRQ-UHFFFAOYSA-N 0.000 abstract 2
- UQXAHKSZLSQVJB-UHFFFAOYSA-N dibutoxy(chloro)borane Chemical compound CCCCOB(Cl)OCCCC UQXAHKSZLSQVJB-UHFFFAOYSA-N 0.000 abstract 2
- RMCBBXAROPWGEZ-UHFFFAOYSA-N ethoxy(oxo)borane Chemical compound CCOB=O RMCBBXAROPWGEZ-UHFFFAOYSA-N 0.000 abstract 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- AQQRXNJMZGAYJW-UHFFFAOYSA-N 2-methylpropoxyboronic acid Chemical compound CC(C)COB(O)O AQQRXNJMZGAYJW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QFKIIWIUGPFUSE-UHFFFAOYSA-N butan-2-yloxyboronic acid Chemical compound CCC(C)OB(O)O QFKIIWIUGPFUSE-UHFFFAOYSA-N 0.000 abstract 1
- NOXNXVPLDITALF-UHFFFAOYSA-N butoxyboronic acid Chemical compound CCCCOB(O)O NOXNXVPLDITALF-UHFFFAOYSA-N 0.000 abstract 1
- LWDVSPMGNLWXKP-UHFFFAOYSA-N chloro(diethoxy)borane Chemical compound CCOB(Cl)OCC LWDVSPMGNLWXKP-UHFFFAOYSA-N 0.000 abstract 1
- CAJRLLAFKJVCQZ-UHFFFAOYSA-N chloro(dipropoxy)borane Chemical compound CCCOB(Cl)OCCC CAJRLLAFKJVCQZ-UHFFFAOYSA-N 0.000 abstract 1
- UVDBJEIOGDVARQ-UHFFFAOYSA-N chloro-bis(2-methylpropoxy)borane Chemical compound ClB(OCC(C)C)OCC(C)C UVDBJEIOGDVARQ-UHFFFAOYSA-N 0.000 abstract 1
- ABTJUWZSOBOMSC-UHFFFAOYSA-N chloro-di(propan-2-yloxy)borane Chemical compound CC(C)OB(Cl)OC(C)C ABTJUWZSOBOMSC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- SNXDIZGWPDHKPR-UHFFFAOYSA-N di(butan-2-yloxy)-chloroborane Chemical compound ClB(OC(C)CC)OC(C)CC SNXDIZGWPDHKPR-UHFFFAOYSA-N 0.000 abstract 1
- SURBAJYBTYLRMQ-UHFFFAOYSA-N dioxido(propan-2-yloxy)borane Chemical compound CC(C)OB([O-])[O-] SURBAJYBTYLRMQ-UHFFFAOYSA-N 0.000 abstract 1
- KUGSJJNCCNSRMM-UHFFFAOYSA-N ethoxyboronic acid Chemical compound CCOB(O)O KUGSJJNCCNSRMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 239000011968 lewis acid catalyst Substances 0.000 abstract 1
- JMVWCCOXRGFPJZ-UHFFFAOYSA-N propoxyboronic acid Chemical compound CCCOB(O)O JMVWCCOXRGFPJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises esters of metaboric acid of the formula <FORM:0815140/IV (b)/1> in which R is an alkyl radical containing 2 or more carbon atoms, preferably 2 to 12 carbon atoms. The novel compounds may be prepared from a dialkyl chloroboronate by heating, preferably at from 150 DEG to 250 DEG C. for 2 to 10 hours and at superatmospheric pressure if required, or by addition of a Lewis acid catalyst, such as ferric chloride or aluminium chloride, preferably in an amount of 0.1 to 10 per cent by weight based on the dialkyl chloroboronate. The esters of metaboric acid may also be prepared by heating an alkyl orthoborate with boron trioxide, preferably in the molar ratio 1 : 1 or with a slight excess of boron trioxide. The heating is suitably effected at a temperature greater than 100 DEG C., preferably in the range 150 DEG to 250 DEG C., and the reaction may be effected at superatmospheric pressure. In examples: (1) ethyl orthoborate and boron trioxide are heated at 250 DEG C. for 10 hours in a sealed glass tube to give ethyl metaborate; (2) diethyl chloroboronate is heated at 250 DEG C. for 10 hours in a sealed tube to give ethyl metaborate; (3) isopropyl orthoborate and boron trioxide are heated for 3 hours under reflux to give iso-propyl metaborate; (4) iso-propyl metaborate is obtained by heating di-iso-propyl chloroboronate at 200 DEG C. for 5 hours; (5) n-propyl metaborate is obtained from n-propyl orthoborate and boron trioxide as in (3); (6) n-propyl metaborate is obtained from di-n-propyl chloroboronate by the procedure of (2); (7) n-butyl orthoborate and boron trioxide are heated at 240 DEG C. for 8 hours to give n-butyl metaborate; (8) n-butyl metaborate is obtained from di-n-butyl chloroboronate by the procedure of (2); (9) di-n-butyl chloroboronate is treated with anhydrous ferric chloride to give n-butyl metaborate; (10) iso-butyl metaborate is obtained from isobutyl orthoborate and boron trioxide by the procedure of (7); (11) isobutyl metaborate is obtained from di-isobutyl chloroboronate by the procedure of (2); (12) sec-butyl metaborate is obtained from sec-butyl orthoborate and boron trioxide as in (7); (13) sec-butyl metaborate is obtained from di-sec-butyl chloroboronate and aluminium chloride by the procedure of (9).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815140A true GB815140A (en) | 1959-06-17 |
Family
ID=1736968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2244457A Expired GB815140A (en) | 1957-07-16 | Improvements in or relating to esters of metaboric acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815140A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1189059B (en) * | 1961-06-14 | 1965-03-18 | Montedison Spa | Process for the production of metaboric acid esters |
| US3253013A (en) * | 1961-06-14 | 1966-05-24 | Montedison Spa | Esters of metaboric acid and process for the preparation thereof |
| DE1227455B (en) * | 1964-04-06 | 1966-10-27 | Stauffer Chemical Co | Process for the preparation of boroxols |
| WO1998042802A1 (en) * | 1997-03-20 | 1998-10-01 | Pilkington Plc | Boroxine compositions |
-
1957
- 1957-07-16 GB GB2244457A patent/GB815140A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1189059B (en) * | 1961-06-14 | 1965-03-18 | Montedison Spa | Process for the production of metaboric acid esters |
| US3253013A (en) * | 1961-06-14 | 1966-05-24 | Montedison Spa | Esters of metaboric acid and process for the preparation thereof |
| DE1227455B (en) * | 1964-04-06 | 1966-10-27 | Stauffer Chemical Co | Process for the preparation of boroxols |
| WO1998042802A1 (en) * | 1997-03-20 | 1998-10-01 | Pilkington Plc | Boroxine compositions |
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